Water → HCID 20300013, compound

HRID 1733699Notes

Reaction equation

HRID 1733699 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(OCC)(=O)C.O>[OH-].[Na+]>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:1][N:2]2[C:6]3[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 1528171-Hydroxy-6-nitrobenzotriazole

Product 1

HCID 20300013HCID 20300013, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (45 ml) is dissolved 1-hydroxy-6-nitro-1,2,3-benzotriazole (7.2 g). To the solution is gradually added p-toluenesulfonyl chloride (7.7 g) with stirring under ice-cooling and further are added thereto ethyl acetate (100 ml) and water (50 ml) and the mixture is stirred for 1 hour. The ethyl acetate layer is separated, dried over magnesium sulfate-charcoal, and concentrated until it becomes about 30 ml. n-Hexane (about 50 ml) is added thereto and the mixture is allowed to stand. The precipitated crystals are separated and dried to give faint yellow needles of 1-(p-toluenesulfonyl-oxy)-6-nitro-1,2,3-benzotriazole (7.5 g), melting point: 142°-144° C. The product is recrystallized from ethyl acetate-n-hexane to give a pure product, melting point: 144° C.

Workup

  1. temperaturecooling
  2. additionfurther are added
  3. customThe ethyl acetate layer is separated
  4. dry with materialdried over magnesium sulfate-charcoal
  5. concentrationconcentrated until it
  6. additionn-Hexane (about 50 ml) is added
  7. customThe precipitated crystals are separated
  8. customdried

Sources & evidence

ORD record
ord-aa7bd18378c64007baaf9587bb7d5edb
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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